NCBI Taxonomy: 3323

Keteleeria (ncbi_taxid: 3323)

found 87 associated metabolites at genus taxonomy rank level.

Ancestor: Pinaceae

Child Taxonomies: Keteleeria davidiana, Keteleeria fortunei, Keteleeria pubescens, Keteleeria evelyniana, Keteleeria hainanensis

(-)-beta-Pinene

Bicyclo(3.1.1)heptane, 6,6-dimethyl-2-methylene-, (1S,5S)-

C10H16 (136.1251936)


(-)-beta-pinene is the (1S,5S)-enantiomer of beta-pinene. It is an enantiomer of a (+)-beta-pinene. (-)-beta-Pinene is a natural product found in Curcuma amada, Molopospermum peloponnesiacum, and other organisms with data available. Flavouring ingredient. (-)-beta-Pinene is found in many foods, some of which are almond, hyssop, sweet bay, and common sage. (-)-beta-Pinene is found in almond. (-)-beta-Pinene is a flavouring ingredient. The (1S,5S)-enantiomer of beta-pinene. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2]. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2].

   

(+)-alpha-Pinene

(R)-(+)--Pinene;(+)--Pinene; (1R)-(+)--Pinene; (1R)--Pinene; (1R,5R)-(+)--Pinene

C10H16 (136.1251936)


alpha-Pinene (CAS: 80-56-8) is an organic compound of the terpene class and is one of two isomers of pinene. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers are known in nature. 1S,5S- or (-)-alpha-pinene is more common in European pines, whereas the 1R,5R- or (+)-alpha-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil (Wikipedia). alpha-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers are known in nature; 1S,5S- or (-)-alpha-pinene is more common in European pines, whereas the 1R,5R- or (+)-alpha-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil. (+)-alpha-pinene is the (+)-enantiomer of alpha-pinene. It has a role as a plant metabolite and a human metabolite. It is an enantiomer of a (-)-alpha-pinene. (+)-alpha-Pinene is a natural product found in Juniperus drupacea, Eucalyptus deglupta, and other organisms with data available. The (+)-enantiomer of alpha-pinene. (1R)-α-Pinene is a volatile monoterpene with antimicrobial activities. (1R)-α-Pinene reduces Bacillus cereus population growth, and exhibits repellent effects[1][2]. (1R)-α-Pinene is a volatile monoterpene with antimicrobial activities. (1R)-α-Pinene reduces Bacillus cereus population growth, and exhibits repellent effects[1][2].

   

alpha-Selinene

4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C15H24 (204.18779039999998)


Occurs in celery oil and hop (Humulus lupulus) oil. alpha-Selinene is found in many foods, some of which are ginger, lovage, sweet bay, and allspice. alpha-Selinene is found in alcoholic beverages. alpha-Selinene occurs in celery oil and hop (Humulus lupulus) oi

   

(+)-Limonene

(4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene

C10H16 (136.1251936)


(+)-Limonene, also known as d-limonene, is a naturally occurring monoterpene which is the major component in orange oil. Currently, (+)-limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Recently, however, (+)-limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to (+)-limonene causes a significant incidence of renal tubular tumours exclusively in male rats. Although (+)-limonene is not carcinogenic in female rats or male and female mice given much higher dosages, the male rat-specific nephrocarcinogenicity of (+)-limonene may raise some concern regarding the safety of (+)-limonene for human consumption. A considerable body of scientific data has indicated that the renal toxicity of (+)-limonene results from the accumulation of a protein, alpha 2u-globulin, in male rat kidney proximal tubule lysosomes. This protein is synthesized exclusively by adult male rats. Other species, including humans, synthesize proteins that share significant homology with alpha 2u-globulin. However, none of these proteins, including the mouse equivalent of alpha 2u-globulin, can produce this toxicity, indicating a unique specificity for alpha 2u-globulin. With chronic exposure to (+)-limonene, the hyaline droplet nephropathy progresses and the kidney shows tubular cell necrosis, granular cast formation at the corticomedullary junction, and compensatory cell proliferation. Both (+)-limonene and cis-d-limonene-1,2-oxide (the major metabolite involved in this toxicity) are negative in vitro mutagenicity screens. Therefore, the toxicity-related renal cell proliferation is believed to be integrally involved in the carcinogenicity of (+)-limonene as persistent elevations in renal cell proliferation may increase fixation of spontaneously altered DNA or serve to promote spontaneously initiated cells. The scientific data demonstrates that the tumorigenic activity of (+)-limonene in male rats is not relevant to humans. The three major lines of evidence supporting the human safety of (+)-limonene are (1) the male rat specificity of the nephrotoxicity and carcinogenicity; (2) the pivotal role that alpha 2u-globulin plays in the toxicity, as evidenced by the complete lack of toxicity in other species despite the presence of structurally similar proteins; and (3) the lack of genotoxicity of both (+)-limonene and d-limonene-1,2-oxide, supporting the concept of a nongenotoxic mechanism, namely, sustained renal cell proliferation (PMID:2024047). (4r)-limonene, also known as (+)-4-isopropenyl-1-methylcyclohexene or (R)-1-methyl-4-(1-methylethenyl)cyclohexene, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (4r)-limonene is considered to be an isoprenoid lipid molecule (4r)-limonene can be found in sweet marjoram, which makes (4r)-limonene a potential biomarker for the consumption of this food product (4r)-limonene can be found primarily in saliva.

   

Pinene

(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene

C10H16 (136.1251936)


Pinene (is a bicyclic monoterpene chemical compound. There are two structural isomers of pinene found in nature: alpha-pinene and beta-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants. Both isomers are used by many insects in their chemical communication system.

   

β-Pinene

(1S,5S)-7,7-dimethyl-4-methylidene-bicyclo[3.1.1]heptane

C10H16 (136.1251936)


An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants. Widely distributed in plants, usually associated with a-Pinene JPV84-W but in smaller amounts. Found in lime peel oil, ginger, nutmeg, mace, bitter fennel, rosemary and sage. Flavour ingredient β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2]. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2].

   

(+)-beta-Caryophyllene

(+)-beta-Caryophyllene

C15H24 (204.18779039999998)


A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has R configuration while the remaining stereocentre has S configuration. It is the enantiomer of (-)-beta-caryophyllene, which occurs much more widely than the (+)-form.

   

Urolignoside

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]oxane-3,4,5-triol

C26H34O11 (522.2101014)


Urolignoside is a natural product found in Salacia chinensis, Keteleeria evelyniana, and other organisms with data available.

   

a-Selinene

4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene

C15H24 (204.18779039999998)


   

80605_FLUKA

Bicyclo(3.1.1)hept-2-ene, 2,6,6-trimethyl-, (1theta)-

C10H16 (136.1251936)


(1R)-α-Pinene is a volatile monoterpene with antimicrobial activities. (1R)-α-Pinene reduces Bacillus cereus population growth, and exhibits repellent effects[1][2]. (1R)-α-Pinene is a volatile monoterpene with antimicrobial activities. (1R)-α-Pinene reduces Bacillus cereus population growth, and exhibits repellent effects[1][2].

   
   

ORANGE TERPENES

ORANGE TERPENES

C10H16 (136.1251936)


   

(4as,7s,8as)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

(4as,7s,8as)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-octahydronaphthalene

C15H24 (204.18779039999998)


   

(1r,2s,6s,7s,8r)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene

(1r,2s,6s,7s,8r)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene

C15H24 (204.18779039999998)


   
   

(4ar,7s)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

(4ar,7s)-1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

C15H22O (218.1670562)


   

(2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4-dimethoxyphenoxy)oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4-dimethoxyphenoxy)oxane-3,4,5-triol

C19H28O12 (448.1580688)


   

2-(hydroxymethyl)-6-{4-[3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

2-(hydroxymethyl)-6-{4-[3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

C26H34O11 (522.2101014)


   

methyl 4-{[(2s,3r,4r,5s,6r)-3-{[(2s,3r,4r,5s,6s)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

methyl 4-{[(2s,3r,4r,5s,6r)-3-{[(2s,3r,4r,5s,6s)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

C21H30O12 (474.173718)


   

2-{4-[7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{4-[7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C25H32O11 (508.1944522)


   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

C25H32O10 (492.1995372)


   
   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]phenoxy}oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]phenoxy}oxane-3,4,5-triol

C24H30O9 (462.18897300000003)


   
   

methyl 4-{[(2s,3r,4r,5s,6r)-3-{[(2s,3r,4r,5s,6s)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxybenzoate

methyl 4-{[(2s,3r,4r,5s,6r)-3-{[(2s,3r,4r,5s,6s)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxybenzoate

C21H30O13 (490.168633)


   

(2s,3r,4s,5s,6r)-2-{4-[(2s,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{4-[(2s,3r)-7-hydroxy-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C25H32O11 (508.1944522)


   

(2r,3r,4s,5s,6r)-2-[(2r)-3-hydroxy-2-{4-[(1s)-1-hydroxypropyl]-2-methoxyphenoxy}propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-[(2r)-3-hydroxy-2-{4-[(1s)-1-hydroxypropyl]-2-methoxyphenoxy}propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C19H30O10 (418.183888)


   

methyl 4-{[(2s,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3-methoxybenzoate

methyl 4-{[(2s,3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3-methoxybenzoate

C21H30O13 (490.168633)


   

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-{4-[(2s,3r)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

C26H34O11 (522.2101014)


   

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4-dimethoxyphenoxy)oxane-3,4,5-triol

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4-dimethoxyphenoxy)oxane-3,4,5-triol

C19H28O12 (448.1580688)